CN103072099B - Acrylate polyurethane chemical mechanical polishing layer - Google Patents

Acrylate polyurethane chemical mechanical polishing layer Download PDF

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Publication number
CN103072099B
CN103072099B CN201210370017.7A CN201210370017A CN103072099B CN 103072099 B CN103072099 B CN 103072099B CN 201210370017 A CN201210370017 A CN 201210370017A CN 103072099 B CN103072099 B CN 103072099B
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isocyanate
chemical mechanical
mechanical polishing
polishing layer
acrylate
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CN201210370017.7A
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CN103072099A (en
Inventor
J·谢
D·B·詹姆斯
C·H·董
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Rohm and Haas Electronic Materials CMP Holdings Inc
Dow Global Technologies LLC
Rohm and Haas Electronic Materials LLC
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Dow Global Technologies LLC
Rohm and Haas Electronic Materials LLC
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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B24—GRINDING; POLISHING
    • B24D—TOOLS FOR GRINDING, BUFFING OR SHARPENING
    • B24D3/00—Physical features of abrasive bodies, or sheets, e.g. abrasive surfaces of special nature; Abrasive bodies or sheets characterised by their constituents
    • B24D3/02—Physical features of abrasive bodies, or sheets, e.g. abrasive surfaces of special nature; Abrasive bodies or sheets characterised by their constituents the constituent being used as bonding agent
    • B24D3/20—Physical features of abrasive bodies, or sheets, e.g. abrasive surfaces of special nature; Abrasive bodies or sheets characterised by their constituents the constituent being used as bonding agent and being essentially organic
    • B24D3/28—Resins or natural or synthetic macromolecular compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09G—POLISHING COMPOSITIONS; SKI WAXES
    • C09G1/00—Polishing compositions
    • C09G1/06—Other polishing compositions
    • C09G1/14—Other polishing compositions based on non-waxy substances
    • C09G1/16—Other polishing compositions based on non-waxy substances on natural or synthetic resins
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B24—GRINDING; POLISHING
    • B24B—MACHINES, DEVICES, OR PROCESSES FOR GRINDING OR POLISHING; DRESSING OR CONDITIONING OF ABRADING SURFACES; FEEDING OF GRINDING, POLISHING, OR LAPPING AGENTS
    • B24B37/00—Lapping machines or devices; Accessories
    • B24B37/11—Lapping tools
    • B24B37/20—Lapping pads for working plane surfaces
    • B24B37/24—Lapping pads for working plane surfaces characterised by the composition or properties of the pad materials
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/4825—Polyethers containing two hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/4854—Polyethers containing oxyalkylene groups having four carbon atoms in the alkylene group
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
    • C08G18/7614—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring
    • C08G18/7621—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring being toluene diisocyanate including isomer mixtures
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
    • H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
    • H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
    • H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
    • H01L21/30—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
    • H01L21/302—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26 to change their surface-physical characteristics or shape, e.g. etching, polishing, cutting
    • H01L21/304—Mechanical treatment, e.g. grinding, polishing, cutting

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Mechanical Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Condensed Matter Physics & Semiconductors (AREA)
  • General Physics & Mathematics (AREA)
  • Manufacturing & Machinery (AREA)
  • Computer Hardware Design (AREA)
  • Microelectronics & Electronic Packaging (AREA)
  • Power Engineering (AREA)
  • Finish Polishing, Edge Sharpening, And Grinding By Specific Grinding Devices (AREA)
  • Mechanical Treatment Of Semiconductor (AREA)
  • Polyurethanes Or Polyureas (AREA)

Abstract

The invention relates to an acrylate polyurethane chemical mechanical polishing layer, specifically to a chemical mechanical polishing pad comprising an acrylate polyurethane polishing layer, wherein the polishing layer exhibits a tensile modulus of 65 to 500 MPa; an elongation to break of 50 to 250%; a storage modulus, G', of 25 to 200 MPa; a Shore D hardness of 25 to 75; and a wet cut rate of 1 to 10 [mu]m/min.

Description

Acrylate urethane chemical mechanical polishing layer
Technical field
The present invention relates to chemical mechanical polishing pads and preparation and application thereof.More specifically, the present invention relates to the chemical mechanical polishing pads comprising acrylate-polyurethane polishing layer, wherein, the stretch modulus of described polishing layer is 65-500MPa; Elongation at break is 50-250%; Storage modulus G' is 25-200MPa; Shore D hardness is 25-75; Wet cutting speed (wet cut rate) is 1-10 [mu.
Technical background
In the manufacture of integrated circuit with other electronic device, need the conductive material of the deposited on silicon multilayer at semiconductor wafer, semi-conducting material and dielectric material, and the surface of these material layers from semiconductor wafer is removed.The thin layer of many kinds of techniques of deposition conductive materials, semi-conducting material and dielectric materials can be used.The chemical vapour deposition (CVD) (PECVD) that in modern wafer processing, conventional deposition technique comprises physical vapour deposition (PVD) (PVD) (also referred to as sputtering), chemical vapour deposition (CVD) (CVD), plasma promote and electrochemistry plating etc.Modern removal technology comprises wet method and dry isotropic and anisotropic etching etc.
When material layer is deposited successively and removes, the uppermost surface of wafer becomes uneven.Because semiconductor machining subsequently (such as metal lining) needs wafer to have smooth surface, so described wafer needs flattened.Complanation can be used to remove the surface topography and blemish, such as rough surface not wishing to occur, agglomerated materials, lattice damage, the layer of cut and pollution or material.
Chemical-mechanical planarization, or chemically mechanical polishing (CMP) are the routine techniques that one is used for carrying out workpiece (such as semiconductor wafer) complanation or polishing.In the CMP of routine, chip support or rubbing head are arranged on bracket component.Described rubbing head is fixed wtih described wafer, described wafer is placed in the position contacted with the polishing layer of polishing pad, and described polishing pad is arranged on estrade in CMP equipment or table top.Described bracket component provides the pressure that can control between wafer and polishing pad.Meanwhile, polishing medium (such as slurries) is dispersed on polishing pad, and introduces in the gap between wafer and polishing layer.In order to carry out polishing, described polishing pad and wafer rotate usually relative to each other.While face rotates polishing pad under the wafer, described wafer scans out the polishing vestige (polishing track) that is generally annular, or polishing area, and the surface of wherein said wafer is directly in the face of described polishing layer.By polishing layer and polishing medium chemistry on a surface of a wafer and mechanism, wafer surface is polished and become smooth.
" finishing " (" conditioning ") of pad interface or " polishing " (" dressing ") is very important for keeping fixing polished surface to obtain stable polishing performance.As time goes by, the polished surface of polishing pad is worn, and has polished micro-texture (microtexture) of polished surface, and this is the phenomenon being called as " blunt (glazing) ".Polishing pad finishing (conditioning) normally completes by using conditioner discs to carry out mechanical lapping to polished surface.Described conditioner discs has coarse refacing, and this coarse refacing is made up of the diamond particles point embedded usually.In a cmp process, when polishing suspends, make conditioner discs contact with polished surface (" outside ") in section in the break time of interval, or carry out in process, making conditioner discs contact with polished surface (" original position ") in CMP.Usual described conditioner discs rotates in the position fixing relative to polishing pad rotating shaft, and the rotation along with polishing pad scans out an annular dressing area.Described trim process goes out miniature raceway groove in pad interface internal cutting, grinds and plane is scraped to the material of polishing pad, again recovers the texture structure of polishing pad.
United States Patent (USP) the 7th, in 169, No. 030, Kulp discloses the polyurethane polishing layer that a class has splendid complanation and defect performance.Kulp discloses a kind of polishing pad comprising polymer substrate, described polymer substrate has top polishing surface, described top polishing surface has polymer polishing concaveconvex structure or forms polymer polishing concaveconvex structure when repairing with abrasive material, described polymer polishing concaveconvex structure extends from polymer substrate and becomes a part for the top polishing surface that can contact substrate polishing process, described polishing pad is by wearing and tearing to top polishing surface or repairing, thus form other polymer polishing concaveconvex structure by polymeric material, overall ultimate tensile strength from the polymer polishing concaveconvex structure of polymeric material is at least 6, 500psi (44.8MPa), overall tearing strength is at least 250 pounds per inch (4.5 × 10 3g/mm).
In the polishing process of semiconductor wafer, realize the conventional polishing layer material flexible relative of low defect, and there is high elongation to break value (>250%).The balance of this character repairs the formation suppressing texture and concaveconvex structure by diamond.
Therefore, people constantly need to have the polishing layer preparation of physical property that is associated well of physical property that can be relevant to low defect preparation, and it also can make described polishing layer have the tailorability (conditionability) of enhancing.
Summary of the invention
The invention provides a kind of chemical mechanical polishing pads, for carrying out polishing to the substrate of at least one be selected from magnetic substrate, optical base-substrate and semiconductor chip, this polishing pad comprises polishing layer, described polishing layer comprises the product of following raw materials according composition: (a) reacts with (ii) prepolymer polyol the isocyanate-terminated polyurethane prepolymer prepared by (i) polyfunctional isocyanate, and wherein said isocyanate-terminated polyurethane prepolymer contains the unreacted NCO group of 4-12 % by weight; (b) polyamines cahin extension agent; The acrylate of c () is selected from (alkyl) acrylic acid hydroxy alkyl ester and (methyl) acrylic acid 2-amino-ethyl ester; And (d) radical initiator, the stretch modulus of described polishing layer is 65-500Mpa; Elongation at break is 50-250%; Storage modulus G' is 25-200Mpa; Shore D hardness is 25-75; Wet cutting speed is 1-10 [mu.
Present invention also offers a kind of preparation method of chemical mechanical polishing pads as claimed in claim 1, it comprises: (a) provides the isocyanate-terminated polyurethane prepolymer of the unreacted NCO containing 4-12 % by weight being reacted preparation by polyfunctional isocyanate and prepolymer polyol; B () provides polyamines cahin extension agent; C () provides the acrylate being selected from (alkyl) acrylic acid hydroxy alkyl ester and (methyl) acrylic acid 2-amino-ethyl ester; D () provides radical initiator; E () is by described isocyanate-terminated polyurethane prepolymer and described crylic acid ester mixture; Described polyamines cahin extension agent is added in the combination of (f) to (e); Described radical initiator is added in the combination of (g) to (f); And (h) causes the polymerization of the combination of (g), form polishing layer.
Present invention also offers a kind of method being used for carrying out substrate polishing, it comprises: the substrate providing a kind of at least one be selected from magnetic substrate, optical base-substrate and semiconductor chip; A kind of chemical mechanical polishing pads as claimed in claim 1 is provided; Dynamic Contact is set up, to carry out polishing to the surface of described substrate between the polished surface and described substrate of polishing layer; And with cutting down device (conditioner), polished surface is repaired.
detailed Description Of The Invention
The polishing layer of chemical mechanical polishing pads of the present invention comprises the product of material composition, described product comprises: (a) reacts with (ii) prepolymer polyol the isocyanate-terminated polyurethane prepolymer prepared by (i) polyfunctional isocyanate, and wherein said isocyanate-terminated polyurethane prepolymer contains unreacted NCO group (the unreacted NCO group of preferred 5-10 % by weight of 4-12 % by weight; More preferably the unreacted NCO group of 5-9 % by weight).Preferably, the number-average molecular weight MW of described isocyanate-terminated polyurethane prepolymer nfor 400-5,000 (is more preferably 400-4,000; Most preferably be 400-2,500); (b) polyamines cahin extension agent; And (c) is selected from the acrylate of (alkyl) acrylic acid hydroxy alkyl ester and (methyl) acrylic acid 2-amino-ethyl ester, wherein, the stretch modulus of described polishing layer is 65-500MPa (preferred 100-350MPa); Elongation at break is 50-250% (preferred 50-150%; More preferably 50-125%); Storage modulus G' is 25-200MPa; Shore D hardness is 25-75 (preferred 30-65; More preferably 40-60); Wet cutting speed is 1-10 [mu (preferred 1-7.5 [mu), and the above results all uses method listed in embodiment and condition to record.Described polishing layer also preferably has the hot strength (being more preferably 10-40MPa) of 5-50MPa, uses method listed in embodiment and condition to record.Described polishing layer also preferably has concaveconvex structure wearing and tearing (in 10 minutes) of <15%, uses method listed in embodiment and condition to record.Described polishing layer also preferably has≤hydrolytic stability of 1.5%, and use method listed in embodiment and condition to record.
Preferably, prepare the polyfunctional isocyanate being used as material composition in the polishing layer of chemical mechanical polishing pads of the present invention and be selected from aliphatic polyfunctional isocyanate, aromatics polyfunctional isocyanate and their mixture.More preferably, described polyfunctional isocyanate is selected from aliphatic vulcabond, aromatic diisocyanates and their mixture.More preferably, described polyfunctional isocyanate is selected from lower group: 1, hexamethylene-diisocyanate (HDI), IPDI (PDI), methylene two (to cyclohexyl (p-cyclohexyl) isocyanates) (H 12mDI), toluene di-isocyanate(TDI) (such as, 2,4-toluene di-isocyanate(TDI), 2,6-toluene di-isocyanate(TDI)), methyl diphenylene diisocyanate, naphthalene diisocyanate (such as, naphthalene-1,5-vulcabond), tolidine diisocyanate, 3,3'-ditolyl vulcabond, diphenyl-4,4'-vulcabond, tetramethyl xylylene diisocyanate, PPDI, xylylene diisocyanate and their mixture.More preferably, described polyfunctional isocyanate is selected from lower group: 2,4-toluene di-isocyanate(TDI), 2,6-toluene di-isocyanate(TDI), methyl diphenylene diisocyanate, naphthalene diisocyanate, tolidine diisocyanate, 3,3'-ditolyl vulcabond, diphenyl-4,4'-vulcabond, tetramethyl xylylene diisocyanate, PPDI, xylylene diisocyanate and their mixture.Most preferably, described polyfunctional isocyanate is selected from 2,4-toluene di-isocyanate(TDI), 2,6-toluene di-isocyanate(TDI)s and their mixture.
Preferably, the prepolymer polyol being used as material composition in the polishing layer of preparation chemical mechanical polishing pads of the present invention is selected from: PPG (such as, polytetramethylene ether diol, polytrimethylene ether glycol), polycarbonate polyol, PEPA (such as, adipic acid second diester, adipic acid fourth diester), polycaprolactone polyol, their copolymer and their mixture.More preferably, described prepolymer polyol is selected from: polytetramethylene ether diol (PTMEG), polytrimethylene ether glycol (PPG), PEPA, polycaprolactone polyol, their copolymer and their mixture.More preferably, described prepolymer polyol is selected from PTMEG, PPG and their mixture.Most preferably, described prepolymer polyol is PTMEG.
Preferably, prepare the polyamines cahin extension agent being used as material composition in the polishing layer of chemical mechanical polishing pads of the present invention to be selected from: 4, 4 '-methylene-two-(2-chloro aminobenzen), 4, 4 '-methylene-two-(3-chloro-2, 6-diethylaniline), diethyl toluene diamine, dimethythiotoluene diamine, 4, 4'-(s-butylamino) diphenyl methane, 3, 3 '-methylene-two (6 amino-, 1, 1-dimethyl esters), 1, ammediol two-(PABA ester), 4, 4 '-methylene-two-(2, 6-diethylaniline), 4, 4 '-methylene-two-(2, 6-diisopropyl aniline), 4, 4 '-methylene-two-(2-isopropyl-6-methylaniline), 2-[2-(2-aminophenyl) sulfanylethyl sulfanyl] aniline, 4, 4 '-methylene-two-(2-chloro aminobenzen), 4, 4-methylene two (N-sec-butyl aniline), triethylenediamine, and their mixture.More preferably, described polyamines cahin extension agent is selected from the polyamines cahin extension agent having and be selected from following general formula:
Wherein, R 1, R 2, R 3and R 4independently selected from hydrogen, C 1-4alkyl and C 1-4alkylthio group.More preferably, described polyamines cahin extension agent is selected from dialkyltoluene diamines (such as, 3,5-dialkyltoluene-2,4-diamines, 3,5-dialkyltoluene-2,6-diamines), two alkylthio group toluenediamines (such as, 3,5-bis-alkylthio group Toluene-2,4-diisocyanate, 4-diamines) and their mixture.More preferably, described polyamines cahin extension agent is selected from diethyl toluene diamine (such as, 3,5-diethyltoluene-2,4-diamines, 3,5-dialkyltoluene-2,6-diamines and their mixture), dimethythiotoluene diamine (such as, 3,5-dimethyl sulphur-based Toluene-2,4-diisocyanate, 4-diamines) and their mixture.More preferably, described polyamines cahin extension agent is selected from 3,5-diethyltoluene-2,4-diamines, 3,5-dialkyltoluene-2,6-diamines, 3,5-dimethyl sulphur-based Toluene-2,4-diisocyanates, 4-diamines) and their mixture.
Preferably, preparing the acrylate being used as material composition in the polishing layer of chemical mechanical polishing pads of the present invention is (C 1-8alkyl) dihydroxypropyl C 1-8arrcostab.More preferably, described acrylate is selected from hydroxyethyl methacrylate (HEMA), hydroxy propyl methacrylate, monomethacrylate polypropylene glycol ester and their mixture.Optimally, described acrylate is hydroxyethyl methacrylate (HEMA).
Preferably, when to prepare the acrylate being used as material composition in the polishing layer of chemical mechanical polishing pads of the present invention be (methyl) acrylic acid 2-amino ethyl ester, the equivalent proportion (NH of unreacted NCO group in the amido in described acrylate and described isocyanate-terminated polyurethane prepolymer 2/ NCO) be preferably 0.1-0.9(more preferably 0.2-0.8, more preferably 0.3-0.7, most preferably 0.4-0.6), the equivalent proportion (NH of unreacted NCO group in the amido in described polyamines cahin extension agent and isocyanate-terminated polyurethane prepolymer 2/ NCO) be preferably 0.9-0.1(more preferably 0.8-0.2, more preferably 0.7-0.3, most preferably 0.6-0.4).Optimally, when described acrylate is (methyl) acrylic acid 2-amino ethyl ester, the equivalent proportion (NH of unreacted NCO group in the amido in described acrylate and described isocyanate-terminated polyurethane prepolymer 2/ NCO) be 0.4-0.6, the equivalent proportion (NH of unreacted NCO group in the amido in described polyamines cahin extension agent and isocyanate-terminated polyurethane prepolymer 2/ NCO) be 0.6-0.4.
Preferably, when the acrylate being used as material composition in the polishing layer preparing chemical mechanical polishing pads of the present invention is (alkyl) hydroxyalkyl acrylates, hydroxyl in described acrylate be preferably 0.1-0.9(more preferably 0.2-0.8 with the equivalent proportion (OH/NCO) of unreacted NCO group in described isocyanate-terminated polyurethane prepolymer, more preferably 0.3-0.7, most preferably 0.4-0.6), the equivalent proportion (NH of unreacted NCO group in the amido in described polyamines cahin extension agent and isocyanate-terminated polyurethane prepolymer 2/ NCO) be preferably 0.9-0.1(more preferably 0.8-0.2, more preferably 0.7-0.3, most preferably 0.6-0.4).Optimally, when described acrylate is (alkyl) hydroxyalkyl acrylates, in hydroxyl in described acrylate and described isocyanate-terminated polyurethane prepolymer, the equivalent proportion (OH/NCO) of unreacted NCO group is 0.4-0.6, the equivalent proportion (NH of unreacted NCO group in the amido in described polyamines cahin extension agent and isocyanate-terminated polyurethane prepolymer 2/ NCO) be 0.6-0.4.
Prepare the radical initiator being used as material composition in the polishing layer of chemical mechanical polishing pads of the present invention and can be selected from various compound, comprise such as, thermal initiator and light trigger.Thermal initiator comprises: such as azo free-radical initiator (such as, 2, 2'-azo two (isobutyronitrile) (" AIBN ") and 2, 2'-azo two (2, 4-methyl pentane nitrile)), and peroxide or perester initator are (such as, benzoyl peroxide, decanoyl peroxide base, lauroyl peroxide, succinic acid peroxide, dicumyl peroxide, 2, 5-bis-(t-butylperoxy)-2, 5-dimethylhexane, t-butylcumyl peroxide, cross octanoic acid ter-butyl ester, di-t-butyl peroxide, cumene hydroperoxide, hydrogen peroxide propyl group (propylhydroperoxide), hydrogen peroxide isopropyl (isopropyl hydroperoxide), tertiary pentyl-2 ethyl hexanoic acid ester, t-amyl peroxypivalate, t-butylperoxy pivarate, peroxide 2 ethyl hexanoic acid tert-pentyl ester, and the peroxide 2 ethyl hexanoic acid tert-butyl ester.Light trigger comprises: such as, 2,2-dimethoxy-2-phenyl acetophenone, 2,2-diethoxy acetophenones, 1-hydroxycyclohexylphenylketone.Those of ordinary skill in the art can select suitable radical initiator with reference to the present invention.
Polishing layer of the present invention, wherein said material composition also optionally comprises diol chain extender.Preferably, described optional diol chain extender is selected from: ethylene glycol, 1,2-propane diols, 1, ammediol (1,3-propylene glycol), 1,3-PD (1,3-propanediol), 1,1,1-trimethylolpropane, 1,2-butanediol, BDO, 1,3-butanediol, 2-methyl isophthalic acid, ammediol, BDO, neopentyl glycol, 1,5-PD, 3-methyl isophthalic acid, 5-pentanediol, 1,6-hexylene glycol, diethylene glycol (DEG), dipropylene glycol, ethoxy resorcinol, quinhydrones two (ethoxy) ether and their mixture.More preferably, described optional diol chain extender is selected from: ethylene glycol, 1,2-PD, 1,3-PD (1,3-propylene glycol), 1,2-butanediol, 1,3-BDO, 2-methyl isophthalic acid, ammediol, 1,4-butanediol, neopentyl glycol, 1,5-pentanediol, 3-methyl isophthalic acid, 5-pentanediol, 1,6-hexylene glycol, diethylene glycol (DEG), dipropylene glycol and their mixture.Most preferably, described optional diol chain extender is selected from: 1,2-butanediol, 1,3-BDO, BDO and their mixture.
The polishing layer of chemical mechanical polishing pads of the present invention can be porous or atresia (namely unfilled) structure.The density of described polishing layer is preferably 0.4-1.3 gram per centimeter 3.The density of porous polishing layer is more preferably 0.5-1 gram per centimeter 3.
Polishing layer of the present invention also optionally comprises a large amount of micro element.Preferably, described a large amount of micro element is evenly dispersed in described polishing layer.Preferably, described a large amount of micro element is selected from: the hollow polymer material of the bubble retained, hollow polymer material, liquid filling, water-soluble material and insoluble phase material (such as, mineral oil).More preferably, described a large amount of micro element is selected from the equally distributed bubble that retains and hollow polymer material in polishing layer.Preferably, the weight average size of described a large amount of micro element is 2-100 micron (15-90 micron).Preferably, described a large amount of micro element comprises and has polyacrylonitrile or polyacrylonitrile copolymer (such as, Expancel tM, purchased from A Ke Nobel company (Akzo Nobel)) the polymeric microspheres of shell wall.
The preparation method of chemical mechanical polishing pads of the present invention comprises: (a) provides isocyanate-terminated polyurethane prepolymer (the unreacted NCO group of preferred 5-10 % by weight of the unreacted NCO containing 4-12 % by weight being reacted preparation by polyfunctional isocyanate and prepolymer polyol; More preferably the unreacted NCO group of 5-9 % by weight); B () provides polyamines cahin extension agent; C () provides the acrylate being selected from (alkyl) acrylic acid hydroxy alkyl ester and (methyl) acrylic acid 2-amino-ethyl ester; D () provides radical initiator; E () is by described isocyanate-terminated polyurethane prepolymer and described crylic acid ester mixture; Described polyamines cahin extension agent is added in the mixture of (f) to (e); Described radical initiator is added in the combination of (g) to (f); And (h) causes the polymerization of the combination of (g), form polishing layer.The preparation method of chemical mechanical polishing pads of the present invention, also optionally comprises: provide diol chain extender; Prepare in (a) in the process of isocyanate-terminated polyurethane prepolymer and add described diol chain extender; And optionally, in (e) before merging with described acrylate, in described isocyanate-terminated polyurethane prepolymer, add described diol chain extender.
Preferably, in the preparation method of chemical mechanical polishing pads of the present invention, the polymerization causing the combination of (g) optionally comprises: heat the combination of (g), or applies electromagnetic energy to the combination of (g).
Preferably, in the preparation method of chemical mechanical polishing pads of the present invention, before the polymerization of combination causing (g), the combination of (g) be transferred in mold cavity (such as injection molding, pressing mold, die sinking) or be transferred to carrier film.
In the preparation method of chemical mechanical polishing pads of the present invention, wherein said acrylate is (methyl) acrylic acid 2-amino ethyl ester; Described acrylate preferably provides with the amount meeting following relation: the equivalent proportion (NH of unreacted NCO group in the amido in described acrylate and described isocyanate-terminated polyurethane prepolymer 2/ NCO) be 0.1-0.9(more preferably 0.2-0.8, more preferably 0.3-0.7, most preferably 0.4-0.6); Described polyamines cahin extension agent preferably provides with the amount meeting following relation: the equivalent proportion (NH of unreacted NCO group in the amido in described polyamines cahin extension agent and described isocyanate-terminated polyurethane prepolymer 2/ NCO) be 0.9-0.1(more preferably 0.8-0.2, more preferably 0.7-0.3, most preferably 0.6-0.4).
In the preparation method of chemical mechanical polishing pads of the present invention, wherein said acrylate is (alkyl) acrylic acid hydroxy alkyl ester, described (alkyl) acrylic acid hydroxy alkyl ester preferably provides with the amount meeting following relation: in the hydroxyl in described acrylate and described isocyanate-terminated polyurethane prepolymer, the equivalent proportion (OH/NCO) of unreacted NCO group is 0.1-0.9(more preferably 0.2-0.8, more preferably 0.3-0.7, most preferably 0.4-0.6), described polyamines cahin extension agent preferably provides with the amount meeting following relation: the equivalent proportion (NH of unreacted NCO group in the amido in described polyamines cahin extension agent and described isocyanate-terminated polyurethane prepolymer 2/ NCO) be 0.9-0.1(more preferably 0.8-0.2, more preferably 0.7-0.3, most preferably 0.6-0.4).
To describe some embodiments of the present invention in detail in the examples below now.
comparing embodiment C1-C4
By the prepolymer (being preheated to 50 DEG C) and 4 by toluene di-isocyanate(TDI) end-blocking listed in table 1,4 '-methylene-two-adjacent chloro aminobenzen (MBCA) (being preheated to 115 DEG C) carries out the polishing layer material mixing to prepare comparing embodiment C1-C4.The ratio of prepolymer used and curing agent is measured by the stoichiometric proportion of amido in NCO group unreacted in prepolymer and MBCA, as shown in table 1.In comparing embodiment C2 and C4, be called by adding commodity in the mixture to prepolymer and MBCA the polymeric microspheres of (purchased from A Ke Nobel company (Akzo-Nobel)) introduces porosity.Added by the type of pore former and % by weight as shown in table 1.Described in use high-speed shearing Mixer is incited somebody to action under the rotating speed of about 3600rpm the mixture of pore former and prepolymer and MBCA combines, and described pore former is evenly distributed in the mixture of described prepolymer and MBCA.Then prepolymer and MBCA(are also comprised for Embodiment C 2 and C4 pore former) final mixture be transferred in mould, and make its gelling about 15 minutes.
Then, described mould is placed in curing oven, uses following thermal cycle to be cured: by the design temperature of the design temperature of curing oven from room temperature to 104 DEG C in 30 minutes; Then the design temperature of curing oven is remained on lower 15 minutes of design temperature or the half an hour of 104 DEG C; Again the design temperature of curing oven is cooled to 21 DEG C, and keeps 2 hours under the design temperature of 21 DEG C.
Then the demoulding of product cake is cut into slices, obtain the polishing layer that thickness is 0.2 centimetre.
table 1
prepolymer is purchased from Chi Mute company (Chemtura).
embodiment 1: the preparation of unfilled polishing layer
By containing 5.8 % by weight unreacted NCO group toluene di-isocyanate(TDI) end-blocking polypropylene glycol prepolymer (830.8 grams) ( lFG 963A, purchased from Chi Mute company (Chemtura)) and HEMA (HEMA) (87.1 grams) add in the container of a gallon.Then in this container, dibutyl tin dilaurate (3 grams) is added.Use eddy mixer under the setting speed of 1,000rpm by the contents stirred 1.5 minutes of container.Add in container again diethyl toluene diamine cahin extension agent (58.1 grams) ( 100-LC, purchased from A Baimaer company ).2,2'-azo two (2-methyl propionitrile) (AIBN) (1 gram is dissolved in 5 milliliters of acetone) is added in container.Then eddy mixer is used under the rotating speed of 1,000rpm by the contents stirred 1 minute of container.The content of container is poured into 66 centimetres x66 centimetre comprise in the pressing mold of 0.2 centimeter apart part.The mould of filling is placed in hot press, and 120 DEG C, solidification 1 hour under pressure condition.Mould is taken out from hot press, and product polishing layer is taken out from mould.
embodiment 2: the preparation of unfilled polishing layer
By containing 8.9 % by weight unreacted NCO group toluene di-isocyanate(TDI) end-blocking poly-(tetramethylene ether) glycol prepolymer (793.3g) ( lF 750D, purchased from Chi Mute company (Chemtura)) and HEMA (HEMA) (124g) add in the container of a gallon.Then in container, dibutyl tin dilaurate (3g) is added.Then eddy mixer is used under the setting speed of 1,000rpm by the contents stirred 1.5 minutes of container.Add in container again diethyl toluene diamine cahin extension agent (82.7g) ( 100-LC, purchased from A Baimaer company ).2,2'-azo two (2-methyl propionitrile) (AIBN) (1g is dissolved in 5mL acetone) is added in container.Then eddy mixer is used under the setting speed of 1,000rpm by the contents stirred 1 minute of container.The content of container is poured into 66 centimetres x66 centimetre comprise in the pressing mold of 0.2 centimeter apart part.The mould of filling is placed in hot press, and 120 DEG C, solidification 1 hour under pressure condition.Mould is taken out from hot press, and polishing layer is taken out from mould.
embodiment 3: polishing layer character
Each embodiment 1-2 neutralization ratio is as shown in table 2 compared with the measurement result of the various character of the polishing layer prepared in Embodiment C 1-C4, that is: hardness (Shore D), hot strength, elongation at break, stretch modulus, toughness, storage modulus G', wet cutting speed, concaveconvex structure wearing and tearing and hydrolytic stability.
The hardness (with Shore D scale) of polishing layer is according to ASTM D2240-05, uses Shore Leverloader(purchased from Instron (Instron)), adopt D type digital standard (Type D digital scale) to carry out measuring.Measure under adopting the load of 4 kilograms to postpone at 15 seconds.
The tensile property of described polishing layer (namely, stretch modulus, hot strength, elongation at break) be according to ASTM D1708-10, use Alliance RT/5 mechanical tester (purchased from MTS Systm Corp.), carry out measuring with the crosshead speed of 2.54 cm per minute.All tests are all that (be set to 23 DEG C, relative humidity be 50%) carries out in the laboratory that temperature and humidity is controlled.Started before 5 days that carry out testing, under all test samples are placed in described experiment condition.The stretch modulus (MPa) of each polishing layer material of reporting, hot strength (MPa) and elongation at break (%) are determined by the load-deformation curve of four parts of repeat samples.
The storage modulus G' of described polishing layer is according to ASTM D5279-08, uses TA instrument ARES flow graph, adopts torsion fixture to carry out measuring.The liquid nitrogen being connected to instrument controls for sub-environment temperature.The linear viscoelasticity response of sample is 1Hz at test frequency, carries out measuring with the heating rate of 3 DEG C/min by-100 DEG C under being warming up to the condition of 200 DEG C.Use 47.5 millimeters of x7 millimeter die heads on Indusco swing hydraulic pressure arm cutting machine to carry out punching press to test sample, form product polishing layer, then by scissor cut to length about 35 millimeters.
The wet cutting speed of described polishing layer and concaveconvex structure wear data use 6ECStrasbaugh polishing tool to measure.This polishing tool comprises and can adapt to 20 the polishing layer sample size of " (~ 51 centimetres) diameter 22 " (~ 56 centimetres) pressing plate.Before carrying out wet cutting speed and concaveconvex structure wear testing, with belt sander, described polishing layer sample is polished, cut into circular pad, according to the circular groove pattern fluting being of a size of 120 mil pitch, 20 mil width, the 20 mil degree of depth, then be layered in (SP2310, purchased from ROHM AND HAAS electronic material CMP Co., Ltd (Rohm and Haas Electronic Materials CMP Inc.)) on foam subpad layer.
For wet cutting speed measurement, use polishing pad finishing dish ( aD3BG-150855 dresser, by Ke Ni can company (Kinik Company) manufacture, purchased from ROHM AND HAAS electronic material CMP Co., Ltd (Rohm and Haas Electronic Materials CMP Inc.)) under following parameter, described polishing layer is worn and torn: duration, by diamond conditioner discs, continuously grinding is carried out 2 hours to described polishing layer; plate speed, 100rpm; slurries, deionized water; slurry flow rate, 150 centimetres 3/ minute; the downward active force of conditioner discs, 62.1kPa.Described wet cutting speed (namely the average groove degree of depth over time) uses to be arranged on the MTI instrument Microtrack II laser triangulation sensor (MTI Instruments Microtrack II Laser Triangulation Sensor) on Zaber science and technology motorization slide block (Zaber Technologies Motorized Slide) and to measure from the pivot of fixing polishing layer to the surface rendering curve of outward flange to polishing layer of polishing layer.The sweep speed of the sensor on slide block (slide) is 0.732 mm/second, and the sampling rate (pendulous frequency/millimeter scanning distance) of sensor is 6.34 point/millimeters.The wet cutting speed reported is depth of groove arithmetic average reducing amount in time, based on the >2 in described polishing layer surface collection, and the thickness measure number of times of 000.
Described concaveconvex structure wear measurement uses to cut the identical polishing layer sample of speed with for measuring to wet, and carries out after described wet cutting rate determination.The object of this test is to study polishing layer material at simulated wafer polishing condition (that is, polishing 8 " diameter Quartz block) and there is no polishing response (glazing response) under the condition of follow-up diamond finishing.Test parameter used is as follows: plate speed, 53rpm; rubbing head speed, 51rpm; downward active force, 27.6kPa (w/6.9kPa back pressure); slurries, ILD 3225(is purchased from Ni Ta-Haas Co., Ltd (Nitta-Haas, Inc.)); slurry flow rate, 150 centimetres 3/ minute; hold the continuous time, 1 minute, 1 minute, 3 minutes and 5 minutes (amounting to 10 minutes).Sample was cut down from described polishing layer with each time interval, Wyko NT8000 optical distribution system (Optical Profiling System) is used (to run vision (Veeco Instruments purchased from Veeco Instrument Ltd., Inc.running Vision), 32 editions, software) carry out optical surface analysis, measure surface roughness compares the reduction (to reduce %) of the roughness of raw material.
The hydrolytic stability that described polishing layer is measured is that the change (in %) of measuring the linear dimension of described sample is determined by room temperature the sample of each polishing layer material being immersed in deionized water 24 hours.
table 2

Claims (10)

1. a chemical mechanical polishing pads, for carrying out polishing to the substrate of at least one be selected from magnetic substrate, optical base-substrate and semiconductor chip, described polishing pad comprises polishing layer, and described polishing layer comprises the product of following raw materials according composition:
A () reacts with (ii) prepolymer polyol the isocyanate-terminated polyurethane prepolymer prepared by (i) polyfunctional isocyanate, wherein said isocyanate-terminated polyurethane prepolymer contains the unreacted NCO group of 4-12 % by weight;
(b) polyamines cahin extension agent,
The acrylate of c () is selected from (alkyl) acrylic acid hydroxy alkyl ester and (methyl) acrylic acid-2-amino-ethyl ester; With
(d) radical initiator,
Wherein, the stretch modulus of described polishing layer is 65-500MPa; Elongation at break is 50-250%; Storage modulus G' is 25-200MPa; Shore D hardness is 25-75; Wet cutting speed is 1-10 [mu.
2. chemical mechanical polishing pads as claimed in claim 1, it is characterized in that, described polyfunctional isocyanate is selected from aliphatic polyfunctional isocyanate, aromatics polyfunctional isocyanate and their mixture.
3. chemical mechanical polishing pads as claimed in claim 1, is characterized in that, described prepolymer polyol is selected from PPG, polycarbonate polyol, PEPA, polycaprolactone polyol, their copolymer and their mixture.
4. chemical mechanical polishing pads as claimed in claim 1, it is characterized in that, described polyamines cahin extension agent is selected from: 4, 4 '-methylene-two-(2-chloro aminobenzen), 4, 4 '-methylene-two-(3-chloro-2, 6-diethylaniline), diethyl toluene diamine, dimethythiotoluene diamine, 4, 4'-bis-(s-butylamino) diphenyl methane, 3, 3 '-methylene-two (6-amino-1, 1-dimethyl esters), 1, ammediol two-(PABA ester), 4, 4 '-methylene-two-(2, 6-diethylaniline), 4, 4 '-methylene-two-(2, 6-diisopropyl aniline), 4, 4 '-methylene-two-(2-isopropyl-6-methylaniline), 2-[2-(2-aminophenyl) sulfanylethyl sulfanyl] aniline, 4, 4 '-methylene-two-(2-chloro aminobenzen), 4, 4-methylene two (N-sec-butyl aniline), triethylenediamine, and their mixture.
5. chemical mechanical polishing pads as claimed in claim 1, it is characterized in that, described acrylate is (C 1-8alkyl) dihydroxypropyl C 1-8arrcostab.
6. chemical mechanical polishing pads as claimed in claim 1, it is characterized in that, described material composition also comprises diol chain extender, described diol chain extender is selected from: ethylene glycol, 1, 2-propane diols, 1, ammediol, 1, ammediol, 1, 1, 1-trimethylolpropane, 1, 2-butanediol, 1, 4-butanediol, 1, 3-butanediol, 2-methyl isophthalic acid, ammediol, 1, 4-butanediol, neopentyl glycol, 1, 5-pentanediol, 3-methyl isophthalic acid, 5-pentanediol, 1, 6-hexylene glycol, diethylene glycol (DEG), dipropylene glycol, ethoxy resorcinol, quinhydrones two (ethoxy) ether, and their mixture.
7. chemical mechanical polishing pads as claimed in claim 1, it is characterized in that, described acrylate is (alkyl) hydroxyalkyl acrylates, and the equivalent proportion (OH/NCO) of unreacted NCO group is 0.1-0.9 in the hydroxyl in described acrylate and described isocyanate-terminated polyurethane prepolymer, and the equivalent proportion (NH of unreacted NCO group in amido in described polyamines cahin extension agent and isocyanate-terminated polyurethane prepolymer 2/ NCO) be 0.9-0.1.
8. chemical mechanical polishing pads as claimed in claim 1, it is characterized in that, described acrylate is (methyl) acrylic acid 2-amino-ethyl ester, and the equivalent proportion (NH of unreacted NCO group in amido in described acrylate and described isocyanate-terminated polyurethane prepolymer 2/ NCO) be 0.1-0.9, and the equivalent proportion (NH of unreacted NCO group in amido in described polyamines cahin extension agent and isocyanate-terminated polyurethane prepolymer 2/ NCO) be 0.9-0.1.
9. prepare a method for chemical mechanical polishing pads as claimed in claim 1, it comprises:
A () provides the isocyanate-terminated polyurethane prepolymer containing the unreacted NCO of 4-12 % by weight being reacted preparation by polyfunctional isocyanate and prepolymer polyol;
B () provides polyamines cahin extension agent;
C () provides the acrylate being selected from (alkyl) acrylic acid hydroxy alkyl ester and (methyl) acrylic acid 2-amino-ethyl ester;
D () provides radical initiator;
E () is by described isocyanate-terminated polyurethane prepolymer and described crylic acid ester mixture;
Described polyamines cahin extension agent is added in the combination of (f) to (e);
Described radical initiator is added in the combination of (g) to (f); And
H () causes the polymerization of the combination of (g), form polishing layer.
10. a method for polishing substrate, it comprises:
The substrate of at least one be selected from magnetic substrate, optical base-substrate and semiconductor chip is provided;
Chemical mechanical polishing pads as claimed in claim 1 is provided;
Dynamic Contact is set up, to carry out polishing to the surface of described substrate between the polished surface and described substrate of polishing layer; And
With cutting down device, polished surface is repaired.
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